Are you looking for the small edges and to go for high risk/high reward? I’ve also heard you had a coin flipping service on 2+2 back in the day?
That depends entirely on your bankroll. I originally had a flipping service on Full Tilt and PokerStars where I would flip anybody. Quickly I changed that into everyone I knew because some players were folding. That of course hurts me a lot so I only did it against trusted players. Those players I would flip against for basically any amount between $2,000 and $10,000 and charge them 1%. I managed to do that for about six months and unfortunately ran very bad at the flips. After that, I increased it to 2% and people weren’t too keen flipping against me anymore. I think it was an okay shot and it’s basically what casinos do. They have a lot more capital reserves than I do, and today I would still do it for 2%, but I don’t think many people would be willing to do it for that.
There’s a lot of variance in it and I wouldn’t recommend it to anyone who can’t handle that variance emotionally. I have had pretty big swings financially and I’m okay with that. I choose to take that on, but I will never get to the point financially where I can’t make back whatever money I have lost doing something like a flipping service. I will always have the money to play in whatever poker games I would like to play myself. The highest stakes that run today are $25/$50 and sometimes $50/$100 so I need enough money to play in those games. After that I don’t think it’s wise to sit on the money you’ve made in excess of that. You want to put that to use.
So what would you be comfortable losing in one day?
I’ve lost 30% of my net worth in one day before. My biggest losing day monetarily was a little over $200,000. I’ve had some big swings, while I prefer not to have those of course. I’ve never gone into a day thinking I was only going to lose $15,000 max and ended up losing $100,000 somehow because my emotions got the better of me. A lot of people get emotional about it and don’t stop when they know they have to. That’s how you go bust.
I have played Rail Heaven a couple of times and I’ve told myself how much I was willing to lose, and after that I would quit. It never got to that point and I ended up running quite all right on Rail Heaven. I knew how much I could lose, and still have money leftover in my bankroll to play my normal games and make the money back. I’m the kind of person who thinks it’s fine to play Rail Heaven for $100,000 with just $300,000 or $250,000 to your name. The question is, can you make back that $100,000 with the $150,000 you have left? When I played Rail Heaven I wasn’t quite that degenerate, but the answer was yes. I would’ve been able to win back that money in case I lost playing on much lower stakes like $25/$50.
You mention the word ‘degenerate’, are there plenty of degenerate things you’ve done in your life?
No, I think the some of the most degenerate things I’ve done are things like playing Rail Heaven with 20% of my net worth on the line. Or maybe things like running a high variance flipping service. I’m the kind of guy who’s taking these high risk/high reward shots, even if it’s for a very significant part of my net worth. I’m just looking at everything from a perspective of, how can I get the biggest ROI? If you’re trying to take this approach it’s very important to have enough money to go back to your normal games.
You’re a very competitive guy and everything you seem to be interested in you put a lot of time into getting very good at. Is that a personality thing that maybe runs in the family?
Yeah I mean there are a lot of things that I inherited and learned from my father. He was very competitive when it came to sports. When I was growing up and I had some obligation or maybe missed a baseball game, I could always tell when the Phillies either won or lost. He’d been doing it for almost 40 years but every single game still had that affect on him. That’s the same way I am, and in addition to that I learned so much from him about how to be a good person and how to respect people. In life you meet so many people and it doesn’t matter what their background or financial situation is, he really taught me to not judge a book by its cover. He also taught me humility, to be happy with what I do and who I am when I wake up in the morning. He loved his job, baseball and I’m fortunate enough right now to do something that I love.
Not judging a book by its cover is something that is extremely hard when you tell someone you’re a poker player, since poker is so easy to judge. Do you think your dad would find it easy to understand why you’ve chosen the path that you’re on right now?
My father was a recreational gambler, and everything he gambled on in life he basically lost money on. He expected to lose, he accepted that and he had fun doing it. Before his passing I had a little success at poker and I was telling him about it. At the time, he didn’t understand how it could be a sustainable long-term thing, and it was the same for my mother. Today she certainly supports what I do, since I’ve been a professional now for over five years. Obviously it’s going well and I don’t think she completely understands it, but she’s finally acknowledges that it’s something that one can do long term.